


Mr Winchester's Office

by LanaVarsi



Category: Supernatural
Genre: 5+1 Things, Anal Sex, Blow Jobs, Bottom Dean, Clothed Sex, Cunnilingus, Established Castiel/Dean Winchester, Established Lisa Braeden/Bela Talbot/Castiel/Dean WInchester, Established Relationship, F/F, F/M, F/M/M, Light Dom/sub, M/M, Multi, Not actually though, Office Sex, POV Original Character, Polyamory, Porn With Plot, Pregnancy Kink, Spit Roasting, Suspected Cheating, Vaginal Sex, Voyeurism, f/f - Freeform, f/m - Freeform, m/m - Freeform
Language: English
Status: Completed
Published: 2020-11-29
Updated: 2020-11-29
Packaged: 2021-03-10 06:13:50
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,014
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27779683
Author URL: https://archiveofourown.org/users/LanaVarsi/pseuds/LanaVarsi
Summary: Lana started her new job as secretary to the CEO of Winchester Restorations, but she soon finds herself trying to understand the various relationships her boss has with the people he fucks, or fuck him, in his office.No actual cheating, and the original character isnotinvolved in the sex.
Relationships: Bela Talbot/Dean Winchester, Castiel/Dean Winchester, Lisa Braeden/Bela Talbot, Lisa Braeden/Castiel/Dean Winchester, Lisa Braeden/Dean Winchester, other relationships mentioned
Kudos: 18





	Mr Winchester's Office

**Author's Note:**

> BTW this is my first smut so IDK how good it is.

**I**  
Lana had admired cars her whole life. Old ones, new ones, it didn’t matter. So the day she was hired for an internship at Winchester Restorations as a bottom of the barrel secretary, was a very good day.

That had been seven years ago. She had now proven herself to be one of the best and brightest secretaries and she had just received her promotion to secretary of the CEO Dean Winchester.

Dean Winchester fascinated her, from his upbringing in small town Kansas to becoming the founder of the worlds most profitable car restoration business in the game to his very personal private life.

It started with an NDA pertaining to any and all information revolving around Mr Winchester, in his professional or personal life, among many other things.

She had never seen the stipulation for personal life before.

On her first full day at her new position she found out why.

Mr Winchester had come into the top floor office that day followed closely by a woman with dark curly hair. The two were walking fast and the woman was clearly not professionally dressed, in a loose button up and a mini skirt.

A few minutes later Lana heard an unexpected sound come through the intercom that she kept on at all times.

“ _Oooohhh fuck,_ ” A woman’s voice moaned.

“ _Yes… Yes… Ohhh fuck, add another,_ ” The voice continued.

There was a louder moan, then, “ _You're gonna have to keep quiet, you don’t want to get caught._ ” That was punctuated with another, louder, moan.

“ _Fuck, baby, _” Cried the girl, “ _I’m ready, I’m ready… Please.”___

___There was a moan that sounded like the combination of the two of them before Lana decided she was too involved to not see this for herself._ _ _

___Lana moved towards the office, checking to make sure she wasn’t in their line of sight. Inside of the office, through the glass walls, Lana could see the woman laying across the desk and Mr Winchester’s back was to the door, so unless the woman took a sudden notion to sit up, Lana was free to watch._ _ _

___The woman had her shirt unbuttoned, exposing her breasts and apparent lack of a bra. Her legs were bent upward with her feet on the desk._ _ _

___Mr Winchester was slowly thrusting into her, head thrown back in ecstasy. From her angle Lana could almost perfectly see her boss’ cock sliding in and out of the wet cunt in front of him._ _ _

___The woman’s skirt hadn’t even been removed, just pushed upwards out of the way. Mr WInchester was still fully dressed with the exception of his unbuttoned pants._ _ _

___Mr Winchester pulled a hand away from the woman’s round hip to pull at one of her nipples, before leaning down and taking the other in his mouth. The woman arched her back, mouth agape._ _ _

___Her boss sped up his thrusts, to the clear pleasure of the woman laying on his desk. She pushed her hips back towards him._ _ _

___When Mr Winchester let go of her nipple with his hand and slowly maneuvered it between him and his partner, pressing and moving along the clit, Lana did the same to herself. She wore dress pants today, but they were a size too big, so she had the stretch._ _ _

___The woman climaxed, falling more limp onto the desk than before; Mr Winchester stood straight up again and continued to thrust into her._ _ _

___Her boss came as well, moaning what she presumed to be the name of the woman._ _ _

___Lana watched as her boss slowly moved his bare cock out of his companion and a small amount of come leaked out of her._ _ _

___Lana went back to work after that, acting as normal as she could when Mr Winchester and Lisa, as she overheard, left his office._ _ _

___**II**  
Lana didn’t have a similar incident for several days. This time it was a dirty blonde woman in a full pantsuit that looked like it cost more then Lana’s rent or a year._ _ _

___“I’m here to see Mr Winchester,” The woman said in a British accent._ _ _

___Lana looked up at the confident smirk the woman had on. “Mr Winchester is not in his office right now, if you’d wish to wait there are couches just down that hall.” Lana pointed in the direction opposite of her boss’ office._ _ _

___“Actually I should be on his personal list,” She purred._ _ _

___“What is your name?” Lana asked knowing that it was part of her job and that this was at least the third security check the woman had to go through, depending on which entrance she took._ _ _

___“Bela Talbot,” The woman even handed her a driver’s license and her security card; clearly she was familiar with the process._ _ _

___Lana verified that she was on the list of people allowed into Mr Winchester’s office no matter what, and checked the two pieces of I.D., seeing that all the boxes had been checked, she let the woman into her boss’ office_ _ _

___Mr Winchester returned no more than ten minutes later._ _ _

___“I let a woman into your office Mr WInchester,” The man raised an eyebrow in question, “A Ms Bela Talbot, sir.”_ _ _

___Her boss smiled lewdly. “Excellent,” He said, “Call down to Trenton in legal, I won’t be making our lunch.”_ _ _

___Lana made the call as instructed after Mr Winchester walked into his office._ _ _

___And just as it had happened days prior, Lana started to hear more NSFW sounds coming from the intercom._ _ _

___It started with a long moan, then Bela asking, “ _Do you want to watch me choke myself on your cock?_ ”_ _ _

___Lana stared at the machine._ _ _

___“ _God yes,_ ” Dean groaned._ _ _

___There was the telltale squeak of an office chair before another long moan from Mr Winchester a moment later._ _ _

___Lana decided to risk watching again; remembering the orgasm she had the day she got home after watching her boss fuck Lisa._ _ _

___She quickly snuck over to the wall that blocked the view of the office from her desk. Lana couldn’t see Bela through the wooden desk, but Mr Winchester had his head thrown back and his hand was moving slowly near his crotch._ _ _

___After many long minutes of watching her boss slowly unravel, he suddenly snapped his head down towards Bela. He said something to the woman and slowly she stood._ _ _

___Bela’s perfect hair was now loose and messy. She leaned forward into Mr Winchester and pushed his chair backwards away from the desk._ _ _

___Bela sat on the boss’s lap, her thighs encasing his, and slowly brought their mouths together. Lana isn’t sure who, but one of them deepened the kiss and slowly Bela started to grind her hips forwards in tandem with their lips._ _ _

___Mr Winchester ran his hands down her sides all of the way until he squeezed her ass with both hands, before sliding them back up and gripping her lean hips._ _ _

___Lana watched as Bela detached herself, she could just barely see Mr Winchester’s wrecked lips, and Bela slowly pulled his shirt off, followed by her own._ _ _

___Bela continued to grind into him as Mr Winchester buried his face in her boobs. Lana slipped a hand under her own shirt and teasingly played with a nipple._ _ _

___Her boss unbuttoned Bela’s pants and felt a hand around her exposed back, before pushing his hands below the waistline and pushing the dress pants down._ _ _

___Bela’s pants were removed, shortly followed by her boss’s._ _ _

___Mr Winchester kissed across Bela’s chest and up her neck until he had his lips beside Bela’s ear. He whispered something as Bela shifted upwards and Lana watched Mr Winchester slowly slip two fingers past Bela’s panties and into her cunt._ _ _

___Bela started to move with his fingers until Mr Winchester added another. Lana finally slipped a finger towards her own clit as her boss pulled his free and grabbed onto Bela’s hips once again._ _ _

___Bela leaned forward then to pull Mr Winchester into a desperate kiss, before lowering herself onto Mr Winchester’s reddened cock. She slowly sank down and Lana slipped a finger fully into herself, thankful for the loose skirt she had worn._ _ _

___As Bela fucked herself on Mr Winchester they kissed and moaned; some even loud enough for Lana to hear._ _ _

___Bela came twice, as far as Lana could tell. The second time was shortly followed by Mr Winchester as he took over the pace of the fucking and snapped his hips into her at a bruising pace._ _ _

___Lana came too, three fingers deep in herself. She slipped away to the bathroom and was seated at her chair in time for Bela to walk out of the office; looking like nothing had happened._ _ _

___**III**  
Lana hadn’t expected her boss to have a relationship, at least the press hadn’t foretold one. But she couldn’t figure out what type of relationship they were._ _ _

___Yesterday was when Bela had first stopped by, but today she was back early in the morning. She only stayed a few moments in Mr Winchester’s office and Lana chidded herself for hoping Bela would be there longer._ _ _

___She hadn’t seen Lisa there since that first day, but she did hear her boss on the phone with someone he referred to as ‘Lis’, so Lana assumed that was her._ _ _

___Lana had taken a short lunch break today, no more than half an hour, to go try a place one of her friends recommended that was close by._ _ _

___When she got back she couldn’t see Mr Winchester at his desk and his office door was opened, so she decided to drop a few files she had printed onto his desk._ _ _

___That was when she heard it._ _ _

___“I love fucking myself on your tight hole,” Growled a deep gravely, very distinctively male, voice._ _ _

___Lana’s jaw dropped as she rounded the corner to see her boss pressed against the far wall of his office with his pants around his ankles and his arms pinned above his head, being fucked into by a tall black haired guy._ _ _

___Lana was close enough to hear the sounds of slick, slapping skin echo out of the room._ _ _

___“Caassss,” Moaned her boss._ _ _

___The man’s hips snapped forward, switching between a teasingly slow pace and a brutal fucking. The man had one hand holding Mr Winchester’s above his head and the one closer to Lana pinching and pulling at one of her boss’s nipples._ _ _

___Mr Winchester moaned with abandon when the man thrusted hard into him at the same time as he pulled on the nipple._ _ _

___After several minutes where Lana stood in plain view of what looked and sounded better than most pornos she had viewed recently she forced herself to move to be at least partially out of view._ _ _

___The man’s dirty talk continues as he fucked into her boss._ _ _

___“ _Fuck, you’re so wet for me._ ”_ _ _

___“ _You love being pounded into by a thick cock, don’t you?_ ”_ _ _

___“ _I’m going to fuck you so hard you’ll feel it as you sit in here all day, reminded of what I did to you._ ”_ _ _

___Eventually the man dropped his hand from Mr Winchester’s nipple and down to his cock. Her boss fell apart shortly after that, followed by the man with several sharp thrusts into a pliant Mr Winchester._ _ _

___Lana slipped back to her desk after that. At the time she had been too shunned and caught off guard to do anything, but that night she replayed the show as she worked her favorite vibrator over her clit._ _ _

___**IV**  
Lana had presumed that there was going to be some long string of hook ups and fuck buddies roll into Mr Winchester’s office after that, but in the following month it was a revolving door involving three people._ _ _

___Lisa usually stopped by in the afternoons, between two and three a couple of times a week._ _ _

___Bela was more random, but it was always in the morning on whatever day she showed up._ _ _

___Cas came by the least often, and he always stayed the longest, usually for a few hours at a time._ _ _

___Lana could never figure out the relationships that were happening in front of her. Mr Winchester never mentioned anything about the three of them to Lana and she never directly asked._ _ _

___They all seemed like more than your usual casual romances though. Lisa and Dean had a six year old son, Bela and Dean had been together since at least their college days, and Dean had met Cas’ brother and sister-in-law as a partner._ _ _

___The three had never even met as far as Lana could tell, and all of the relationships they shared with Mr Winchester seemed to be progressing further._ _ _

___Lana almost slapped herself when she finally saw it one day. Mr WInchester wore a ring, on his left ring finger to be specific. She noticed it before but had never actually _seen_ it, somehow._ _ _

___“Are you married Sir?” She asked tentatively one afternoon._ _ _

___Mr Winchester smiled down at the ring. “About eight years now,” He said and offered no further information._ _ _

___To whom?_ _ _

___Was it one of the three or did he actually have someone waiting for him at home?_ _ _

___Lisa was by again that afternoon, she was Lana’s pick for the most probable spouse of Mr Winchester. The already had a son and based on the fucking without condoms and dirty talk, Lana assumed they were trying for another._ _ _

___“ _Fuck,_ ” Came her boss’s voice through the intercom, “ _I’m gonna fuck another baby into you. Fill you with my hot come until your round with my kid._ ”_ _ _

___Lisa moaned and loudly proclaimed her agreement to the idea._ _ _

___Lana didn’t watch that day, it felt too intimate even though Mr Winchester was fucking her over his desk. That didn’t stop her from listening though, it was hot and dirty talk was a major kink of Lana’s._ _ _

___Lana heard them get redressed before Lisa said, “ _It’ll work Babe, until then we just have to keep trying._ ”_ _ _

___**V**  
Lisa had, since starting work three months ago, started wearing skirts everyday. And keeping an extra pair of panties in her purse. She barely needed porn anymore, not that porn was entirely female oriented, she just had to recall what she had witnessed while at work._ _ _

___She had her preferences though for what she liked with each one._ _ _

___Lisa and Mr Winchester was usually the most intimate and sensual; there was a major check beside pregnancy kink there though._ _ _

___Bela and Mr Winchester were a lot rougher, but they still knew exactly what the other liked and were very enthusiastic; check beside consent kink there._ _ _

___Cas (full name Castiel) and Mr Winchester was slightly leaned towards dom/sub but only when Cas topped, which happened most of the time; she could have told someone when she met her boss that he was a bottom but whatever._ _ _

___Somehow, after three full months, none of them had ran into each other. At least not in the office._ _ _

___That was until one fateful day when Mr WInchester had a meeting that would run from noon until after the workday had officially ended._ _ _

___Bela was on that day, she gave Mr Winchester a blow job before he went down to the office followed by a series of kisses that could only have riled him back up. She then sat on Mr Winchester’s desk facing the skyline out the window as Lana filed a large stack of documents._ _ _

___Then, for the first time even, Lisa showed up early._ _ _

___The dark haired woman had walked by Lana enough times on her way into Mr Winchester’s office that she just smiled and gave her a small wave as she passed._ _ _

___Lana cranked the volume on her intercom, hoping to hear whatever was about to happen. It was not what she expected._ _ _

___From her chair Lana could see the door open, and she was bracing herself for confrontation before, “ _Babe, you know he’s in a meeting today._ ” _ _ _

___Lana’s head whipped around to the intercom like it held some sort of answers. That was Bela speaking. Apparently she and Lisa knew each other._ _ _

___“ _Maybe that’s why I’m here,_ ” Lisa purred, far too close to the intercom to be anywhere except touching Bela._ _ _

___Bela gasped playfully. “ _You want to play around in his office when he’s not here?_ ”_ _ _

___“ _That’s why you waited isn’t it?_ ” Lisa teased._ _ _

___There was a pause, then Lana heard the telltale breathy moans and wet sounds of kissing._ _ _

___“ _I know,_ ” Bela panted, “ _I suggested it- uuhhh- but I d-didn’t think you’d go for it._ ”_ _ _

___Bela moaned again, clearly Lisa was doing something to her._ _ _

___“ _You remember how horny I was last time I got pregnant,_ ” Lisa said plainly._ _ _

___Lisa was pregnant? Was it Mr Winchester’s? How long had she and Bela been doing this? Did Mr Winchester know?_ _ _

___“ _Fuckk,_ ” Bela pressed out, “ _That wasn’t until l-later on though. You were showing, I remember- uugh- remember it quite fondly._ ”_ _ _

___“ _Keep making sounds like that Babe,_ ” Lisa encouraged through a moan of her own, “ _God you taste good. And I was, you were just out of town most of the first semester last time._ ”_ _ _

___“ _And Dean was hogging y-you,_ ”_ _ _

___Lana jumped. Did that mean Mr Winchester knew about them, was this a threeway thing?_ _ _

___“ _You’re not the only one with a pregnancy kink,_ ” Lisa reminded._ _ _

___There wasn’t much talking after that. Bela continued to moan loudly, and Lisa eventually joined in. Lana heard Bela come and then what Lana presumed was the two of them switching places, and Lisa came a few minutes later._ _ _

___Lana had to leave before Mr Winchester’s meeting was over that day; she contemplated just making her brother get a cab, but with taxi fares here in New York she knew he would make her pay and bitch about it for his whole two days in town._ _ _

___**VI**  
She took the following day off to hang out with her brother and when she arrived at the office nothing seemed off with Mr Winchester. As per usual she didn’t ask._ _ _

___By lunch she hadn’t seen Bela, but that wasn’t unusual._ _ _

___Lisa showed up after two. She was wearing a skirt that was actually quite similar to the one Lana was sporting. Lisa passes her with the same smile and wave before entering Mr Winchester’s office._ _ _

___Lisa and Mr WInchester always have the most foreplay, he seems to have a love for making her moan and get wet before he touches her pussy._ _ _

___When she hears footsteps round the corner, Lana mutes the intercom._ _ _

___A second later she is greeted with Cas in his usual trench coat and suit. The suit is loose and wrinkled but Lana knows her suits and knows it costs more than her car back home._ _ _

___He doesn’t acknowledge her as he passes, he rarely does. Once he’s out of earshot Lana switches the intercom back on._ _ _

___Lisa was moaning as the office door opened, there was no way to know what Mr Winchester was doing to her at that point but Lana still had images to recall._ _ _

___For a second there was silence before the sound of thick fabric hitting the desk close to Mr Winchester’s intercom, then Lisa moans again._ _ _

___“ _Fuck, yesssss,_ ” Was all Lisa said, before, “<>God, will one of you just finger me already?_”_ _

__Lana stared wide eyed at the intercom as the sound of two men’s laughter was shortly drowned out by a loud moan from Lisa._ _

__After a few minutes of panting and moans from all three people in the office, Mr Winchester asks, “ _How do you want us Sweetheart?_ ”_ _

__There's shuffling, clothes hit the floor, and the desk is moved. After the moans and panting resume, Lana finally cracks and moves towards the office._ _

__Lana is not disappointed by the view when she gets there._ _

__Lisa is naked except for a stringy lace bra, and is laying on her stomach across the short side of the desk. Mr Winchester is slowly fucking her pussy from the closer side of the desk and Cas is slowly pushing into her mouth._ _

__It continues for what feels like hours. Lana has never been someone that's big on spit roasting, but Lisa looks damn near perfect laying across the dark oak desk._ _

__Lisa comes after Cas starts to fuck her throat and Dean gets a hand on her clit._ _

__Mr Winchester comes deep in her cunt a few minutes later._ _

__Cas pulls out of her mouth and moves around the desk until he pushes into her already come soaked pussy._ _

__Lisa and Cas come at the same time after he thrusts into her several times._ _

__Lana slips back to her desk, content in knowing that she had something to think back on that night when she was alone with her toys._ _

__Cas and Lisa leave about half an hour later. Lisa doesn’t wave to Lana but she presumes that is because Lisa is wrapped around Cas’ arm._ _

__“ _Lana,_ ” She hears over the intercom. Suddenly she’s more worried, “ _Come in here for a moment please._ ”_ _

__When Lana enters his office Mr Winchester is leaning back in his desk chair, the one Lana had seen him come on multiple times, looking at her solemnly._ _

__“I’m sure you know why you are in here?” He asked._ _

__Lana didn’t respond, instead she nodded. She was pretty sure she knew where this was going._ _

__Mr Winchester smiled sadly at her. “You definitely earned the promotion you were given, you do great work, but…”_ _

__Lana hung her head in shame. She knew what she was doing was wrong but it was too good to resist._ _

__“I didn’t mind at first,” He said, surprising Lana, “Watching us was okay when you did it a few times, I’ve gotten off watching my partners go at it so I can’t really blame you. But it’s not something that can continue.”_ _

__Lana sighed. “I’ll just pack my stuff,” She said meekly._ _

__“Hey,” Mr Winchester called as she started to turn away, “I said I didn’t blame you, and I really don’t. But you can’t exactly work in this office anymore._ _

__“Your contract was originally for six months. So I’ll give you the next two and a half off at full pay and that should give you enough time to find adequate arrangements in Detroit.”_ _

__“Detroit?” She asked, shocked._ _

__“You’ll be transferring to the office there. It’s the same pay and same position, just a different city. That's okay?”_ _

__Lana nods enthusiastically. Mr Winchester tells her the rest of the necessary information, but right before he dismissed her, she turned around. With a contemplating glance she said, “You know I have to ask.”_ _

__Mr Winchester smiled, somewhat bashfully. “About the four of us?” She nodded. “We’re all together. Been married just over eight years, and no it’s not legal so technically Lis and I are married and Cas and Bela, but we had a fancy double wedding and commitment ceremony.”_ _

__“Wow,” Was all she could manage. “This might be too personal but, you and Lisa have a kid and are expecting another. Why just the two of you?”_ _

__“Don’t worry, others have asked. Bela likes kids but doesn’t want to deal with being pregnant and all of that, which: reasonable, and Cas’ family is loaded and could do any number of things if he had children of his own.”_ _

__“How loaded?” She asked sheepishly._ _

__“We’re all well off; I’ve got this company, which I’m sure you know is well known; Lisa has yoga studios in most major cities along with classes for the public and wealthy, she also co-owns LiVie active wear; Bela is an art curator that specializes in occult works, she’s the highest in her field; and Cas is the second son of Chuck and Anna Novak, billionaires extraordinaire._ _

__“And I haven’t shared anything personal, at least that you haven’t already heard,” He pointed to the intercom on his desk, “Or anything you could find with a quick Google. Now why don’t you get going. And please remember that the NDA you signed lasts the next fifteen years.” Mr Winchester smiled. Lana left his office happily, ready to start her (voyeurism free) job in Detroit._ _

**Author's Note:**

> Sorry about the plot at the end, I couldn't help myself.
> 
> Also this is unBetaed (cause no one can know it exists) so feel free to leave corrections below.
> 
> Also Also Actually Actually, what did you think of this? I haven't personally read anything that similar.


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